


Extra Credit

by Rachrar



Series: Hat Academy [1]
Category: Villainous (Cartoon)
Genre: M/M, Making a mess on a desk, Spreader Bars, Teacher-Student Relationship, Trans Flug (Villainous), like god guys clean up
Language: English
Status: Completed
Published: 2017-09-20
Updated: 2017-09-20
Packaged: 2018-12-31 21:00:44
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,485
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12141039
Author URL: https://archiveofourown.org/users/Rachrar/pseuds/Rachrar
Summary: Flug failed a test for the third time, and he really needed to pass or his scholarship would be revoked. Luckily, Headmaster Black Hat of a villain's college wasn't above letting his students pass by alternative methods.





	Extra Credit

**Author's Note:**

> This is a gift for lovely drawinggheys (tumblr) for showing such lovely Professor Black Hat pics in the Discord and when we got thirsty CONTINUING TO DRAW MORE! The amazingness boggles the mind, honestly.

Flug packed up his backpack, struggling not to cry on the test sitting on the desk. The large circled F taunted him; it was honestly the first failure he had gotten in his life, and of course he would have it in the one class taught by the eldritch headmaster. Naturally. Because failing a class taught by a human would be too easy. It had to be Headmaster Black Hat.

Flug hoisted his bag, throwing it over his shoulder. He planned on going to the afterclass meeting to hopefully find out how he could improve his score and pass the class, but when he looked around, he was the only one there apart from the professor. May as well ask right now, then, he supposed.

He made his way down the aisles, catching Black Hat’s attention. The eldritch piqued a brow, curious. Once Flug was in casual speaking distance, he coughed awkwardly to break the silence. “U-uhm, sir?”

Black Hat set down the pile of papers he had been organizing, gaze unwavering on the paperbag wearing student. “Spit it out, I don’t have all day.”

“R-right sir, sorry.” Flug took a deep breath. “I, ah, I failed the test. For the third time. And I’m failing. Is there anything I can do for extra credit? Or to make up the difference? I really need to pass, my scholarship--”

Black Hat waved his hand to shut the boy up. He didn’t care why, though losing the scholarship Flug had would mean losing money, and that was his life’s motivation. That wouldn’t do-- though just passing him would not work either.

“Anything?” Black Hat repeated, mind searching for how to let Flug improve his score, making and dismissing ideas as soon as they went through his head.

“Y-yes sir! Please!” Flug’s earnest agreement gave Black Hat pause, eyes sliding to meet the young man’s. The desperation was palpable, and Black Hat knew that Flug had no idea what he was proposing. “I’ll clean after class, or-- or do the menial work like grading quizzes, I just really need to improve my grade!”

Black Hat snorted. “I have aids for that.” Flug’s shoulders sank. What else could he offer that the headmaster wouldn’t already have?

“I… I’ll do anything you want, sir…” Flug said quietly, his eyebrows so sweetly upturned and expression so painfully innocent that it made something in Black Hat’s stomach twist. It was  _ disgusting. _ Flug was in a college for villains, what was he doing being so-- so-- eugh,  _ honest? _

Black Hat leaned on the podium, gaze as sharp as his mint teeth. “You’ll do anything, anything at all?”

Flug shifted his weight from foot to foot. “Yes,” he swallowed down his discomfort at the leer Black Hat gave him. He was probably going to clean the laboratory, or have to deal with the mess in the cells after the experiments concluded. It was filthy and just the idea made him shiver.

Black Hat stared at him for a long moment, testing his resolve. Nervous, but determined, Flug kept eye contact the entire time. Shockingly, Black Hat was the one to break it, turning to the papers once more and gathering them.

“Come to my office this evening at 9.” Flug blinked. That wasn’t the normal office hours. The normal hours were from 2 to 3 pm every other day.

He didn’t question him, though, just nodding. The questions burned but the need to pass was much, much stronger, and he kept his curiosity to himself. Black Hat inclined his head just slightly, a kinder dismissal than Flug had ever received from the professor before. Taking the hint, he scurried out, checking his watch. He had a lot of time to kill.

\---

At 8:59:52, Flug stood before the door, hand raising to knock. Just before his hand made contact, the door swung open to reveal Black Hat, grinning down at Flug. “Punctual to an extreme degree, aren’t we?” he mocked, but stepped aside nonetheless for Flug to enter.

The office was cleaner than previous times he’d seen it; in fact, there was only the desk and its accompanying chair, but there was a box he had never seen in the seat. “Hello, H-Headmaster,” Flug answered, easing into the room. “I didn’t want to keep you waiting.”

“Good.” Black Hat closed the door behind Flug, then took the box and set it on the table, sitting in the chair like a king on a throne.

Flug didn’t see another seat, so he just stood unsurely, setting his bag down near the desk. “I-- uhm, where am I going to sit, sir?”

Black Hat’s smirk grew, pointing to the floor before him. More confused than ever, but obeying anyway, Flug slowly moved to kneel in front of Black Hat. “S-sir? I’m confused. What’s going on?”

“Simple.” Black Hat widened his stance, knees nearly closing around Flug’s shoulders. “You’re going to blow me and we’ll figure out what to do for your grades depending on how well you do.”

Flug recoiled, trying to stand but was forced down by Black Hat’s magic holding him to the floor. “Sir! That’s--”

_ “Villainous?” _ Black Hat hissed dangerously.

Flug wavered, then lowered back to the floor, feet protesting the position. “... Yes, sir.” His hands balled up on his thighs and lowering his head, ashamed to realize that his boxers were a touch damp. He  _ may _ have fantasized about this once or twice. Or every time he saw the professor, if he was honest.

“So get to it!” Black Hat napped his fingers and his clothing vanished entirely, leaving him bare of everything but the eponymous hat. Between his legs was a plump slit, a small, wriggly tendril peeking out.

Flug licked his lips, pushing the bag up just enough to free his jaw, glad that paper folds so easily. It helped that he always carried extras in his bag, just in case. He was scared he’d mess up and just piss Black Hat off, but he was game to try at least.

He scooted forward, hands hovering over Black Hat’s thighs for a moment before resting lightly on them, then lapped gently at the wiggling organ. It grew, spreading the lips as it extended out towards his mouth, plunging inside and ruthlessly thrusting into his throat.

Flug gagged, pulling away in shock and coughing into his hand. His eyes watered, wiping them away before glaring at Black Hat, who just grinned smugly. Huffing, but prepared now, Flug went back to work. As innocent as he seemed compared to the majority of the villain college, he wasn’t a virgin by any means. Sex, and the related acts, were some of the few things he was confident in, as much as he didn’t look it.

He swallowed the tentacle to the hilt, throat spreading naturally and easily now that he was prepared. The pointed tip squirmed and rolled in pleasure, and Black Hat inhaled sharply, nails clawing into the armrests. Flug felt a certain satisfaction at the reaction, shifting as his jeans rubbed against his clit roughly certainly helping the feeling along.

Black Hat growled, curling over Flug and releasing the armrests to grasp at Flug’s head. He was careful not to tear the bag, but certainly held Flug tightly in place. His clawed toes dug into the carpeted floor, giving leverage for him to roll his hips and fuck Flug’s throat. Flug swallowed the pre dripping from the tip, moaning at a particularly rough thrust. His eyes fluttered, wanting more, so much more.

He pulled off with difficulty, panting. His hand had begun to rub against himself, whining. He laid his head on Black Hat’s thigh, eyes looking up to him in need, biting his lip.

“Oh, you filthy creature…” Black Hat caressed Flug’s face. Flug turned to kiss at it, laving the fingers with his tongue, sucking gently at the sharp claw.

Flug’s lips curled into a triumphant smile. “Are you going to  _ punish _ me, sir?”

Black Hat’s eyes widened for a moment, pupils expanding from their cat-like slits. “You’d like that, wouldn’t you?”

Flug nuzzled at the slimy tentacle, uncaring of the sticky mess it was making on his skin. Black Hat’s lips tightened at the brazen display before him. Incredible.

“Am I in  _ detention?” _ Flug mocked, hand sliding up and down the wiggly tendril, his other hand rubbing desperately at his jeans. “Are you going to slap me with a ruler?”

Black Hat stood suddenly, shoving the chair behind him to crash into the wall. Flug jumped, worried that he had made a mistake and began scrambled backwards. Black Hat stepped on Flug’s labcoat, ceasing Flug’s motion.

“Stay still.” Pausing to get a nod from Flug, he turned to the box he had set aside, opening it. He turned around, a soft silk tie in hand. The matte fabric was monogrammed with a silk BH in the center, a subtle addition to the expensive fabric. “Over the desk.”

Flug blinked in surprise, then grinned. “Yes, Professor.” He stood, kicking his shoes off and unabashedly ridding himself of his pants and boxers. A hesitation, then he pulled the bag off, though he kept the goggles on. His dark hair covered the majority of his face, a remarkable case of helmet hair from the bag, but Black Hat left it be. He’d see the nerd’s face at some point later, right now he was focused on that wet cunt on display as Flug bent over the desk, the plump lips just begged to be spread wide around a fat cock.

Flug’s usual nervousness returned, realizing he had never made it clear that he was trans. What if Black Hat wasn’t into vagina-havers? Oh dear… He sputtered mid-thought when he felt a long, wriggly tongue slip inside his pussy, seeking out his g-spot with remarkable precision. His hand slammed on the table, going on tip toes and rocking against it, Black Hat’s hands holding his thighs apart to better eat him out. Black Hat buried his face in Flug’s cunt, letting his tongue explore every nook and cranny within.

“S-sir!” Flug squealed, hand riding to cover his mouth, moaning like a wanton whore on display. A ruler slapped down near his head, rattling against the wood for a moment before stilling, Black Hat reveling in Flug’s shaky jump.

“Don’t cover your mouth.” With that, Black Hat returned to Flug’s cunt. His thumbs spread Flug’s cheek wide, glad for his noseless nature so he could really get up in there, nuzzling against the heated folds and flicking his tongue over Flug’s enlarged clit. Flug moaned, forcing his hand to stay on the desk, nails digging into the wood.

“Good boy,” Black Hat purred, the vibrations of his voice traveling all the way through Flug’s core much like the snakelike tongue flicking around Flug’s pussy.

“Oh, fuck, sir!”

Black Hat pulled away at the curse, picking up the discarded ruler. Flug whined, beginning to rise to turn, but Black Hat slammed his front back down, fingers spreading over Flug’s lower back to keep him in place. 

“Language,” he crooned malevolently, gently into Flug’s ears, watching the young man squirm. Claws picked up the ruler, tapping the table. “Hands flat, where I can see them.”

Flug swallowed, a lump in his throat, and shakingly put his hands where indicated. He would have been worried about actual trouble, had Black Hat not chosen that moment to lean over him, purposely grinding against Flug. The cool, almost cold, tentacle writhed around Flug’s cunt lips, threatening to push inside but always slipping past at the last moment.

The ruler came down on Flug’s knuckles, making him screech, hands jerking to his chest from the pain, whimpering.  “I-I’m sorry!”

“You will be.” Black Hat leaned back, grinding into Flug, his cock stiff and still just so he could rut between Flug’s labia, each ridge making Flug’s breath hitch.

“Sir, please--!” Black Hat pulled away entirely, rustling through the box. A moment later and he was fitting cuffs around Flug’s ankles. Flug looked down; they were attached to a spreader bar. Oh-- oh dear.

“You come to me, begging, and you still cannot stop asking for more.  _ Selfish. _ ” Black Hat swung the ruler, hitting Flug’s ass with the flat of the wood. Flug yelped, but it warbled off into a moan, and he leaned forward, gripping on the back edge of the desk and presenting his ass for more. Black Hat was surprised, but he was more than pleased to take advantage.

He slammed the ruler down again and again, watching the skin redden under his assault, then slowly welt up. Flug was screaming each time he was touched, tears filling his goggles and his chest heaving with cries. As much as he yelled in pain, however, he just got wetter, especially when Black Hat aimed a (lighter) slap on his cunt lips. By the time Black Hat dropped the ruler, his ass was liberally sprinkled with bruises and his slick was sliding down his legs in rivulets, his testosterone engorged clit visibly throbbing for release.

“Do you want more?” Black Hat rubbed at the heated flesh. Flug stifled a sob, shaking his head. He removed the goggles with weak hand, setting it aside, but within arms reach as a security measure.

“P-please, I need-- I need you i-i-in me!” Flug reached back to stroke at Black Hat’s cock, a pathetic keening heard even over the lewd slaps of Flug’s hand. Black Hat growled, slapping Flug’s hand away.

“Would you give up getting off if I gave you an A?” Black Hat’s fingers traced around Flug’s entrance, sticky pre latching onto his claws greedily,

Flug flat out sobbed, resting his forehead against the desk, hips following every motion. Words were nearly beyond his grasp, his pussy  _ aching _ to be filled. He felt so empty, like he had never felt before, needing that ridged, constantly moving cock to fill him to the brim, bring down his fever with cold flesh lest he burn away entirely. 

“Y-yes,” he managed through hiccups, ready to fall apart if he had to say more. Black Hat cut through the chain of the spreader bar, freeing Flug.

_ “Good boy.” _ Black Hat thrust his dick inside in one swift push, and Flug  _ wailed _ , hitting the desk in an attempt to control his sounds and screaming, then biting his hand in a futile try, but he was too loud and his voice still echoed in the office.

Black Hat’s pace was brutal, and the position they were in was not conducive to the rough pounding he longed to give with how Flug’s skinny hips kept hitting the edge of the desk. Flug might be too aroused to notice, but Black Hat did; so he fixed it. He grabbed Flug’s right leg, pulling it up for it to rest on the desk. The new angle let him get deeper, and if Flug’s incoherent screeches were to be believed, it was worth it.

He left his cock soften just enough to get squirmy again, adjusting the shape so it would rub right up against Flug’s g-spot with every movement. Flug was beyond noise at this point, panting and trying to keep enough air in his lungs to prevent hyperventilating, the feeling too good to even express. He gave up on it, merely along for the ride.

He felt his orgasm approaching, the tight muscles in his abdomen so close to that crucial point. He couldn’t speak, just gagging out some vague noises to try and tell Black Hat, but Black Hat just stopped. Flug was ready to meet death at that point if he got cock-blocked  _ again _ , but luckily for him, Black Hat just spun him around, having him straddle the eldritch. Black Hat’s arms were tight around Flug, tentacles giving stability rather than any physical surface, fucking Flug into the air like he weighed nothing.

Flug’s nails dug into Black Hat’s shoulders, biting and kissing, hoping to get Black Hat to that same precipice he danced along. Black Hat bit on Flug’s shoulder, careful not to bite through fabric. Flug was tight as a vice around him, almost to the point of being unable to move; he was pulling Flug down on his dick as much as he was thrusting up.

With one last thrust, Flug exploded, squirting his orgasm over Black Hat hard enough that the eldritch felt Flug’s arousal slowly but surely dribbling down his leg. Black Hat shoved Flug down just a few more times, one last deep thrust into the warm walls of Flug’s cunt and he burst with a heady splurt assailing Flug’s deepest core with his cum, the dense, viscous goo squeezing out of Flug to splat on the floor. Black Hat held Flug in the air for a long minute more, then slowly set him down on the desk on his stomach, uncaring of the mess made when they separated. Their mingled cum was going to stain, but neither of them thought of that.

Black Hat made sure Flug wasn’t going to fall over, Flug loose limbed and soft, but holding himself up well enough that Black Hat released him a moment later. He turned to the floor, the open box and the assorted toys inside abandoned. The tie too, sadly. He just had to make Flug squeal, and when it came to Flug, he was hard pressed to say that the experience was lacking anything, even if all he’d used was the spreader bar. But the mental image of Flug struggling to try and close his legs while Black Hat was spanking him was going to linger in all the best ways.

Black Hat opened a drawer, pulling out a stack of papers, then kicked the box from the chair, sitting on it a moment later. Crossing his legs as if it were perfectly normal to be naked and grading classwork with a well fucked student slowly coming back to this plane of reality nearby, Black Hat waited for Flug to regain his voice.

Pausing after a moment, he weaved his hand in the air, a soda appearing in his claws, then offered it to Flug. Flug took it shakily, popping the seal and taking a drink with a grateful sigh. As Flug’s shakes lessened, Black Hat worked through the essays, snorting at some of the drivel they thought was acceptable, and stamping large failing grades on over half of them.

By the time Flug had worked though the soda, he was steady. He stretched, muscles protesting, but the deep ache in them was satisfying. He wriggled his way to stand, wrinkling his nose at the still dripping cum from his cunt. Messy and disgusting.

Black Hat snapped his fingers to get Flug’s attention. He pointed to the desk again. “On your belly.”

Confused, Flug did as he was told, bending over the desk. Black Hat set the papers down, and as he stood, his clothing reformed around his body, looking dapper and as if the past couple hours hadn’t happened.

Black Hat knelt behind Flug, parting his cheeks. Surprisingly gently, his tongue slithered inside, cleaning Flug out in soft laps. Flug mewled; the motions were too light and he was too tired to get aroused so quickly, yet the action seemed intimate in a way that was more vulnerable than the sex.

Faster than Flug would have expected, Black Hat was done, licking around his mouth to get the remaining fluid. He straightened, giving Flug a gentle slap on the ass just to watch him flinch and whimper at the pain. “Get dressed and out you go. I expect to see you in office hours at least once a week.”

Flug did as he was told, trying to figure out whether he passed the class or not from the enigmatic words. “Yes, sir. I-- I’ll see you Friday at 2 then?”

Black Hat barked out a laugh. “No, you fool. Here at 9 again. A grade is an ongoing process to raise, you know. Can’t just turn it around with one meeting.” Flug’s eyes widened as he realized what Black Hat meant, blushing a pretty crimson under the bag. “Is that a problem?”

“No, sir!” Flug chirped, grabbing his backpack. “I’ll see you every Tuesday and Th-Thursday! Gotta keep the knowledge fresh in my mind, r-right, Professor?”

“Headmaster,” Black Hat correctly, but his voice held no true rebuke. “Now go be good and do whatever it is humans do when they aren’t wasting oxygen in my office.”

Flug bounced out of the door, his joy radiating as brightly as the sun. It was almost sweet, if it wasn’t disgustingly sweet. Black Hat picked up the discarded and replaced paper bag, folding it carefully and tucking it in the desk. Flug wasn’t going to be able to visit every day, after all, and Black Hat was nothing if not insatiable.


End file.
